2-({2-[(Naphthalen-1-ylmethyl)amino]ethyl}amino)ethanol | 892566-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-({2-[(Naphthalen-1-ylmethyl)amino]ethyl}amino)ethanol
• 英文别名: 2-[2-(naphthalen-1-ylmethylamino)ethylamino]ethanol
• CAS: 892566-55-1
• 化学式: C₁₅H₂₀N₂O
• 分子量: 244.337
• InChiKey: QMTFLSJRQQJKGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-({2-[(Naphthalen-1-ylmethyl)amino]ethyl}amino)ethanol 在 sodium tetrahydroborate 、 戴斯-马丁氧化剂 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 59.0h， 生成
  参考文献：
  名称：

  One-Dimensional Random Walk of a Synthetic Small Molecule Toward a Thermodynamic Sink

  摘要：

  We report on the spontaneous intramolecular migration of alpha-methylene-4-nitrostyrene from amine group to amine group along oligoethyleneimine tracks up to eight repeat units in length (number of amine footholds, n = 3, 5, 9). Each track consists of n - 1 aliphatic secondary amine footholds plus a naphthylmethylamine group foothold situated at one end of the track. Under basic conditions the alpha-methylene-4-nitrostyrene unit undergoes a series of reversible intramolecular Michael-retro-Michael reactions between adjacent amine groups that move it up and down the track. For n = 3 and 5 it is possible to monitor the population of every positional isomer on the track by H-1 NMR spectroscopy. On the longest track (n = 9) the fraction of walkers on each end-foothold can be quantified with respect to those on the inner footholds. In all cases the naphthylmethylamine foothold acts as a thermodynamic sink with the steady-state distribution significantly biased in favor of the walker at that site. The dynamics of the walker migration is well described by the random walk of a Brownian particle in one dimension.

  DOI：

  10.1021/ja402382n
• 作为产物：
  描述：

  1-萘甲醛 在 sodium tetrahydroborate 、 戴斯-马丁氧化剂 作用下， 以 乙醇 为溶剂， 反应 19.0h， 生成 2-({2-[(Naphthalen-1-ylmethyl)amino]ethyl}amino)ethanol
  参考文献：
  名称：

  One-Dimensional Random Walk of a Synthetic Small Molecule Toward a Thermodynamic Sink

  摘要：

  We report on the spontaneous intramolecular migration of alpha-methylene-4-nitrostyrene from amine group to amine group along oligoethyleneimine tracks up to eight repeat units in length (number of amine footholds, n = 3, 5, 9). Each track consists of n - 1 aliphatic secondary amine footholds plus a naphthylmethylamine group foothold situated at one end of the track. Under basic conditions the alpha-methylene-4-nitrostyrene unit undergoes a series of reversible intramolecular Michael-retro-Michael reactions between adjacent amine groups that move it up and down the track. For n = 3 and 5 it is possible to monitor the population of every positional isomer on the track by H-1 NMR spectroscopy. On the longest track (n = 9) the fraction of walkers on each end-foothold can be quantified with respect to those on the inner footholds. In all cases the naphthylmethylamine foothold acts as a thermodynamic sink with the steady-state distribution significantly biased in favor of the walker at that site. The dynamics of the walker migration is well described by the random walk of a Brownian particle in one dimension.

  DOI：

  10.1021/ja402382n

文献信息

• One-Dimensional Random Walk of a Synthetic Small Molecule Toward a Thermodynamic Sink
  作者：Araceli G. Campaña、David A. Leigh、Urszula Lewandowska

  DOI：10.1021/ja402382n

  日期：2013.6.12

  We report on the spontaneous intramolecular migration of alpha-methylene-4-nitrostyrene from amine group to amine group along oligoethyleneimine tracks up to eight repeat units in length (number of amine footholds, n = 3, 5, 9). Each track consists of n - 1 aliphatic secondary amine footholds plus a naphthylmethylamine group foothold situated at one end of the track. Under basic conditions the alpha-methylene-4-nitrostyrene unit undergoes a series of reversible intramolecular Michael-retro-Michael reactions between adjacent amine groups that move it up and down the track. For n = 3 and 5 it is possible to monitor the population of every positional isomer on the track by H-1 NMR spectroscopy. On the longest track (n = 9) the fraction of walkers on each end-foothold can be quantified with respect to those on the inner footholds. In all cases the naphthylmethylamine foothold acts as a thermodynamic sink with the steady-state distribution significantly biased in favor of the walker at that site. The dynamics of the walker migration is well described by the random walk of a Brownian particle in one dimension.